- Carboxylation with CO2 via brook rearrangement: Preparation of α-hydroxy acid derivatives
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In the presence of CsF, a wide range of α-substituted α-siloxy silanes were carboxylated under a CO2 atmosphere (1 atm) via Brook rearrangement. A variety of α-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford α-hydroxy acids in moderate-to-high yields. One-pot synthesis from aldehydes using PhMe2SiLi and CO 2 was also possible, providing α-hydroxy acids without the isolation of an α-hydroxy silane.
- Mita, Tsuyoshi,Higuchi, Yuki,Sato, Yoshihiro
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- SOLUBLE EPOXIDE HYDROLASE INHIBITORS
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Disclosed are alpha keto amide and alpha hydroxy amide compounds and compositions that inhibit soluble epoxide hydrolase (sEH), methods for preparing the compounds and compositions, and methods for treating patients with such compounds and compositions. The compounds, compositions, and methods are useful for treating a variety of sEH mediated diseases, including hypertensive, cardiovascular, inflammatory, pulmonary, and diabetic-related diseases.
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Page/Page column 114; 115
(2008/12/06)
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- Cyclic alkyl substituted glycolides and polylactides therefrom
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Cyclic alkyl, particularly cyclohexyl, substituted glycolides and polylactides are described. The polylactides have a high glass transition temperature and improved clarity.
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Page/Page column 6
(2008/06/13)
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- An efficient new synthesis of racemic cetiedil and a novel route to α-ketocarboxylic acids utilising mild conditions
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We describe a new efficient synthesis of the prescribed racemic drug cetiedil [(±)-2-cyclohexyl-2-(3-thienyl)ethanoic acid 2-(hexahydro-1H-azepin-1-yl)ethylester], Additionally, we report herein a high yielding large scale, route to its acid precursor 7, subsequently enabling large-scale synthesis of the chiral forms of cetiedil, and detailed pharmacological investigations. Additionally, we describe a novel route to α-ketocarboxylic acids, starting from readily available or easily obtainable aldehydes: The mild conditions utilised opens up its applicability for use on molecules of biological interest. Georg Thieme Verlag Stuttgart.
- Roxburgh, Craig J.,Ganellin, C. Robin,Thorpe, Andrew J.
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p. 1211 - 1214
(2008/02/07)
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- Samarium diiodide-promoted diiodomethylation of carbonyl compounds with iodoform. Synthetic applications of diiodoalcohols
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A rapid and effective diiodomethylation of carbonyl compounds using SmI2 and iodoform is described. Transformations of the obtained diiodoalcohols 2 into α-iodoaldehydes 5 and α-hydroxyacids 6 is also reported.
- Concellon, Jose M.,Bernad, Pablo L.,Perez-Andres, Juan A.
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p. 1409 - 1412
(2007/10/03)
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- Reaction of carboxylic acids with diethyl phosphorocyanidate; a novel synthesis of homologated α-hydroxycarboxylic acids from carboxylic acids
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Carboxylic acids react with 2 equivalents of diethyl phosphorocyanidate in the presence of triethylamine to give dicyanophosphates in good yields; these dicyanophosphates can be hydrolyzed easily to give homologated α- hydroxycarboxylic acids.
- Mizuno, Masanori,Shioiri, Takayuki
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p. 9209 - 9210
(2007/10/03)
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- Dienediolates of Unsaturated Carboxylic Acids in Synthesis. Synthesis of Cyclohexenones and Polycyclic Ketones by Tandem Michael-Dieckmann Decarboxylative Annulation of Unsaturated Carboxylic Acids.
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Substituted 2-cyclohexenones 4 to 7 and hexahydronaphthalenones and hexahydroindenones 13 to 18 are prepared by tandem Michael-Dieckmann addition of lithium dienediolates of acyclic and alicyclic unsaturated carboxylic acids to the lithium salts of the same or other unsaturated carboxylic acids.
- Aurell, Maria J.,Gavina, Pablo,Mestres, Ramon
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p. 2571 - 2582
(2007/10/02)
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- 1-Chloroalkyl p-Tolyl Sulfoxides as Useful Agents for Homologation of Carbonyl Compounds: Conversion of Carbonyl Compounds to α-Hydroxy Acids, Esters, and Amides and α,α'-Dihydroxy Ketones
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One-carbon homologation of carbonyl compounds to α-hydroxy acids, esters, and amides by the use of 1-chloroalkyl p-tolyl sulfoxide as a hydroxycarbonyl anion equivalent is reported.Oxidation of the vinyl chlorides, the intermediates of the above-mentioned
- Satoh, Tsuyoshi,Onda, Ken-ichi,Yamakawa, Koji
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p. 4129 - 4134
(2007/10/02)
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